CA2143571A1

CA2143571A1 - Oxydes et sulfures de bisacylphosphine dimere

Oxydes et sulfures de bisacylphosphine dimere

Info

Publication number: CA2143571A1
Authority: CA; Canada
Prior art keywords: formula; c4alkyl; substituted; production; c4alkoxy
Prior art date: 1994-03-02
Legal status : Abandoned

Application number

CA002143571A

Other languages

English (en)

Inventor

David G. Leppard

Manfred Kohler

Current Assignee

BASF Schweiz AG

Original Assignee

Individual

Priority date

1994-03-02

Filing date

1995-02-28

Publication date

1995-09-03

1995-02-28 Application filed by Individual filed Critical Individual

1995-09-03 Publication of CA2143571A1 publication Critical patent/CA2143571A1/fr

Status Abandoned legal-status Critical Current

Links

150000003568 thioethers Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 95
-1 sulfides Compounds Chemical class 0.000 claims abstract description 76
229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
239000001301 oxygen Substances 0.000 claims abstract description 11
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
239000011593 sulfur Substances 0.000 claims abstract description 5
239000000203 mixture Substances 0.000 claims description 108
238000000576 coating method Methods 0.000 claims description 73
238000004519 manufacturing process Methods 0.000 claims description 63
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
229910052739 hydrogen Inorganic materials 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 40
239000011248 coating agent Substances 0.000 claims description 37
239000000460 chlorine Substances 0.000 claims description 35
238000000034 method Methods 0.000 claims description 35
229910052801 chlorine Inorganic materials 0.000 claims description 34
229910052736 halogen Inorganic materials 0.000 claims description 31
150000002367 halogens Chemical class 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
150000002431 hydrogen Chemical group 0.000 claims description 25
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 24
239000000843 powder Substances 0.000 claims description 22
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 19
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 19
239000000758 substrate Substances 0.000 claims description 19
229910052731 fluorine Inorganic materials 0.000 claims description 17
239000000463 material Substances 0.000 claims description 15
238000007639 printing Methods 0.000 claims description 15
230000008569 process Effects 0.000 claims description 15
229910052751 metal Inorganic materials 0.000 claims description 14
239000002184 metal Substances 0.000 claims description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000003973 paint Substances 0.000 claims description 13
125000001624 naphthyl group Chemical group 0.000 claims description 12
125000006839 xylylene group Chemical group 0.000 claims description 12
239000006185 dispersion Substances 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
229920002120 photoresistant polymer Polymers 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
235000010290 biphenyl Nutrition 0.000 claims description 10
239000004305 biphenyl Substances 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000002131 composite material Substances 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 10
239000000654 additive Substances 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
239000002023 wood Substances 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
239000000976 ink Substances 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
239000000049 pigment Substances 0.000 claims description 7
238000007650 screen-printing Methods 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
239000006096 absorbing agent Substances 0.000 claims description 5
239000000853 adhesive Substances 0.000 claims description 5
230000001070 adhesive effect Effects 0.000 claims description 5
238000005538 encapsulation Methods 0.000 claims description 5
238000011049 filling Methods 0.000 claims description 5
YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
230000001678 irradiating effect Effects 0.000 claims description 4
PDLPMGPHYARAFP-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C(=O)C1=CC=CC=C1 PDLPMGPHYARAFP-UHFFFAOYSA-N 0.000 claims description 3
ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical class OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims description 3
NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical class OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 claims description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
230000000996 additive effect Effects 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 24
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 17
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 3
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
238000006116 polymerization reaction Methods 0.000 abstract description 4
238000001723 curing Methods 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 17
229920001577 copolymer Polymers 0.000 description 17
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
230000005855 radiation Effects 0.000 description 13
150000003254 radicals Chemical class 0.000 description 13
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 12
229920000642 polymer Polymers 0.000 description 12
238000009472 formulation Methods 0.000 description 11
239000010410 layer Substances 0.000 description 11
239000000178 monomer Substances 0.000 description 11
229920000728 polyester Polymers 0.000 description 11
229920005862 polyol Polymers 0.000 description 11
150000001252 acrylic acid derivatives Chemical class 0.000 description 10
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
150000003077 polyols Chemical class 0.000 description 9
239000000047 product Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229920005989 resin Polymers 0.000 description 7
239000011347 resin Substances 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 6
239000003365 glass fiber Substances 0.000 description 6
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
229910052753 mercury Inorganic materials 0.000 description 6
150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
238000000016 photochemical curing Methods 0.000 description 6
229920000647 polyepoxide Polymers 0.000 description 6
229920002635 polyurethane Polymers 0.000 description 6
239000004814 polyurethane Substances 0.000 description 6
QBJOHXRRAKMFIH-UHFFFAOYSA-N (2,4,6-trimethylbenzoyl)phosphanyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)PC(=O)C1=C(C)C=C(C)C=C1C QBJOHXRRAKMFIH-UHFFFAOYSA-N 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000003848 UV Light-Curing Methods 0.000 description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
239000002585 base Substances 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
150000001735 carboxylic acids Chemical class 0.000 description 5
238000009833 condensation Methods 0.000 description 5
230000005494 condensation Effects 0.000 description 5
239000000975 dye Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000000465 moulding Methods 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
229910000073 phosphorus hydride Inorganic materials 0.000 description 5
229920003023 plastic Polymers 0.000 description 5
239000004033 plastic Substances 0.000 description 5
239000000600 sorbitol Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
239000004952 Polyamide Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
239000002253 acid Substances 0.000 description 4
150000003926 acrylamides Chemical class 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000012964 benzotriazole Substances 0.000 description 4
BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000011093 chipboard Substances 0.000 description 4
150000001805 chlorine compounds Chemical class 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
150000002009 diols Chemical class 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
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125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000007788 liquid Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
238000007645 offset printing Methods 0.000 description 4
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
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125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000007787 solid Substances 0.000 description 4
HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
229920006305 unsaturated polyester Polymers 0.000 description 4
229920006337 unsaturated polyester resin Polymers 0.000 description 4
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 3
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229910052783 alkali metal Inorganic materials 0.000 description 3
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IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
229940093475 2-ethoxyethanol Drugs 0.000 description 2
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